diff --git a/jetty-core/jetty-osgi/src/main/java/org/eclipse/jetty/osgi/OSGiApp.java b/jetty-core/jetty-osgi/src/main/java/org/eclipse/jetty/osgi/OSGiApp.java
index 5f2fa1fad017..fb71c6985fd9 100644
--- a/jetty-core/jetty-osgi/src/main/java/org/eclipse/jetty/osgi/OSGiApp.java
+++ b/jetty-core/jetty-osgi/src/main/java/org/eclipse/jetty/osgi/OSGiApp.java
@@ -29,6 +29,7 @@
 import org.eclipse.jetty.server.Deployable;
 import org.eclipse.jetty.server.handler.ContextHandler;
 import org.eclipse.jetty.util.StringUtil;
+import org.eclipse.jetty.util.URIUtil;
 import org.eclipse.jetty.util.resource.Resource;
 import org.eclipse.jetty.util.resource.ResourceFactory;
 import org.osgi.framework.Bundle;
@@ -80,7 +81,7 @@ private static Resource getBundleAsResource(Bundle bundle) throws Exception
         File bundleLocation = BundleFileLocatorHelperFactory.getFactory().getHelper().getBundleInstallLocation(bundle);
         File root = (bundleOverrideLocation == null ? bundleLocation : new File(bundleOverrideLocation));
         //Fix some osgiPaths.get( locations which point to an archive, but that doesn't end in .jar 
-        URL url = BundleFileLocatorHelperFactory.getFactory().getHelper().getLocalURL(root.toURI().toURL());
+        URL url = BundleFileLocatorHelperFactory.getFactory().getHelper().getLocalURL(URIUtil.correctURI(root.toURI()).toURL());
         
         return ResourceFactory.root().newResource(url);
     }
diff --git a/jetty-core/jetty-osgi/src/main/java/org/eclipse/jetty/osgi/util/Util.java b/jetty-core/jetty-osgi/src/main/java/org/eclipse/jetty/osgi/util/Util.java
index 27ea01b2d64a..b97afbddfd2e 100644
--- a/jetty-core/jetty-osgi/src/main/java/org/eclipse/jetty/osgi/util/Util.java
+++ b/jetty-core/jetty-osgi/src/main/java/org/eclipse/jetty/osgi/util/Util.java
@@ -29,6 +29,7 @@
 
 import org.eclipse.jetty.osgi.OSGiServerConstants;
 import org.eclipse.jetty.util.StringUtil;
+import org.eclipse.jetty.util.URIUtil;
 import org.osgi.framework.Bundle;
 import org.osgi.framework.BundleContext;
 import org.osgi.framework.Filter;
@@ -61,7 +62,7 @@ public static URI resolvePathAsLocalizedURI(String path, Bundle bundle, Path jet
             return null;
 
         if (path.startsWith("file:/"))
-            return new URI(path);
+            return URIUtil.correctURI(new URI(path));
 
         if (path.startsWith("/") && File.separatorChar != '/')
             return new URI("file:" + path);
diff --git a/jetty-ee10/jetty-ee10-webapp/src/main/java/org/eclipse/jetty/ee10/webapp/WebInfConfiguration.java b/jetty-ee10/jetty-ee10-webapp/src/main/java/org/eclipse/jetty/ee10/webapp/WebInfConfiguration.java
index f1ee27e818a1..19e6819cbaf2 100644
--- a/jetty-ee10/jetty-ee10-webapp/src/main/java/org/eclipse/jetty/ee10/webapp/WebInfConfiguration.java
+++ b/jetty-ee10/jetty-ee10-webapp/src/main/java/org/eclipse/jetty/ee10/webapp/WebInfConfiguration.java
@@ -204,19 +204,24 @@ public void unpack(WebAppContext context) throws IOException
                     !webApp.isDirectory()
             )
             {
-                // Look for sibling directory.
                 Path extractedWebAppDir = null;
 
+                // If this is a war file, we should look for a sibling
+                // directory of the same name where it has been already extracted
                 if (war != null)
                 {
-                    Path warPath = context.getResourceFactory().newResource(war).getPath();
-
-                    // look for a sibling like "foo/" to a "foo.war"
-                    if (warPath != null && FileID.isWebArchive(warPath) && Files.exists(warPath))
+                    // We have obtained the webApp from the war string, so it
+                    // cannot be a CombinedResource, therefore safe to use it's Path
+                    Path warPath = webApp.getPath();
+                    if (warPath != null)
                     {
-                        Path sibling = warPath.getParent().resolve(FileID.getBasename(warPath));
-                        if (Files.exists(sibling) && Files.isDirectory(sibling) && Files.isWritable(sibling))
-                            extractedWebAppDir = sibling;
+                        // look for a sibling like "foo/" to a "foo.war"
+                        if (FileID.isWebArchive(warPath) && Files.exists(warPath))
+                        {
+                            Path sibling = warPath.getParent().resolve(FileID.getBasename(warPath));
+                            if (Files.exists(sibling) && Files.isDirectory(sibling) && Files.isWritable(sibling))
+                                extractedWebAppDir = sibling;
+                        }
                     }
                 }
 
diff --git a/jetty-ee9/jetty-ee9-webapp/src/main/java/org/eclipse/jetty/ee9/webapp/WebInfConfiguration.java b/jetty-ee9/jetty-ee9-webapp/src/main/java/org/eclipse/jetty/ee9/webapp/WebInfConfiguration.java
index ccb0ad828510..8420bdccc002 100644
--- a/jetty-ee9/jetty-ee9-webapp/src/main/java/org/eclipse/jetty/ee9/webapp/WebInfConfiguration.java
+++ b/jetty-ee9/jetty-ee9-webapp/src/main/java/org/eclipse/jetty/ee9/webapp/WebInfConfiguration.java
@@ -207,18 +207,24 @@ public void unpack(WebAppContext context) throws IOException
                     !webApp.isDirectory())
             )
             {
-                // Look for sibling directory.
                 Path extractedWebAppDir = null;
 
+                // If this is a war file, we should look for a sibling
+                // directory of the same name
                 if (war != null)
                 {
-                    Path warPath = Path.of(war);
-                    // look for a sibling like "foo/" to a "foo.war"
-                    if (FileID.isWebArchive(warPath) && Files.exists(warPath))
+                    // We have obtained the webApp from the war string, so it
+                    // cannot be a CombinedResource, therefore safe to use it's Path
+                    Path warPath = webApp.getPath();
+                    if (warPath != null)
                     {
-                        Path sibling = warPath.getParent().resolve(FileID.getBasename(warPath));
-                        if (Files.exists(sibling) && Files.isDirectory(sibling) && Files.isWritable(sibling))
-                            extractedWebAppDir = sibling;
+                        // look for a sibling like "foo/" to a "foo.war"
+                        if (FileID.isWebArchive(warPath) && Files.exists(warPath))
+                        {
+                            Path sibling = warPath.getParent().resolve(FileID.getBasename(warPath));
+                            if (Files.exists(sibling) && Files.isDirectory(sibling) && Files.isWritable(sibling))
+                                extractedWebAppDir = sibling;
+                        }
                     }
                 }